Mashable

In the first decade of the 20th century, the words "hep" and "hip" were used interchangeably to mean “aware.” The precise origin of the words is unknown, though one theory suggests slaves from Senegal used the word xipi (pronounced "hippy" or "hippeh" in the native Wolof language), which means “to have your eyes open and be aware."

Calling someone hip or hep became a way to note their sophistication, coolness or knowledge of fashion. It was particularly prevalent in the world of jazz, where the coolest and most in-the-know characters were called "hepcats." In 1939, Cab Calloway published his lexicon of jazz vernacular, Cab Calloway's Hepster’s Dictionary: Language of Jive, a pun on Webster’s Dictionary. "Hepster" came to mean a white fan of jazz.

If one person can be identified as the first hipster, it might be Harry Gibson, born Harry Raab in the Bronx in 1915. Growing up around Harlem, Raab adopted jive talk, and became a proficient and energetic jazz pianist in speakeasies.

In 1939, Fats Waller recruited him as his intermission act, and Raab lifted a new stage name, Gibson, off a gin bottle.

For the next six years, he studied music at Juilliard during the day and played at various jazz clubs along the “Swing Street” stretch of 52nd Street at night. During this period, he started calling out to his audience as “hipsters,” and soon adopted the appellation for himself, with his original song “Handsome Harry the Hipster."

They call him Handsome Harry, the Hipster /
He's the ball with all the chicks /
He plays piano like mad, his singing is sad /
He digs those mellow kicks

Harry Gibson, "Handsome Harry the Hipster"

April 1947

Image: William P. Gottlieb/Library of Congress

Gibson’s bouncing boogie woogie playing and manic stage presence garnered him loyal audiences, and he became noted for his original songs, which featured risqué lyrics about sex and drug use. The latter was a constant in Gibson’s life, which contributed to his career decline after 1947, when he recorded “Who Put the Benzedrine in Mrs. Murphy’s Ovaltine?”

He flew under the radar in the following decades, before staging a comeback with two albums in the late 1980s, replete with characteristically naughty lyrics about strip clubs, skinny-dipping and smoking reefer.

After falling ill with congestive heart failure, Gibson decided to take his own life. He shot himself on May 3, 1991.

Image: Delmark Records

April 1947

Image: William P. Gottlieb/Library of Congress

I'm famous for singing wild jazz tunes and playing wild rocking piano and really tearing up the joint, I was practically the first person to ever do that shit. Then came rock and roll and they all did that shit, but nobody did that stuff before me.

Harry Gibson

April 1947

Image: William P. Gottlieb/Library of Congress

Visit Premier Exhibitions at 417 5th Avenue to see the past become present again at "Retronaut's New York." This pop-up exhibition of extraordinary, digitally restored photographs captures New York City at the turn of the 20th century. It's only open until March 28, so be sure to get down there before it’s gone.